I was selling my cigarettes outside Union Station and no one was buying them. It was the only commodity I had to sell before grabbing a piece of cardboard, writing something witty on it and panhandling for change. 

I spent every night drunk in New York and barely survived in Boston and Philadelphia. I was out of money and I needed at least a few dollars to get to my hostel and think about what I could do to pay for it. 

After my unsuccessful attempt at finding cash I began the long walk to the hostel on the other side of the city. 

I checked the map on my phone, my destination was well over an hour away. 

To add to my current state of shit luck, my phone battery was dying, the snow had started and for the first 20 minutes I was heading in the wrong direction. 

After I turned around and had begun to march in the right direction I spotted an L station and decided to give it a go. 

I had tried the same thing earlier to no avail. 

‘Maybe it will work this time.’ I thought to myself. 

I slid my card in the machine and hoped for the best. The ticket exited the machine and the last few dollars in my bank account vanished. I had a train. 

I secured some emergency funds at the hostel once I reconnected with the world through the magic of WiFi and paid the cunty looking people at the front desk. 

There was something very cunty about this hostel that I had gone through such bullshit to be in. 

There were real cunty people doing real cunty things in this real cunty hostel. 

I stayed in this cunty hostel located far away from the main action of Chicago for a few days and then changed to one in Wicker Park. I couldn’t let Chicago turn out as dull as the last few weeks had been. This was Chicago, I had to make this stop count. 

I arrived in Wicker Park, checked in and went up to the rooftop for the view of Chicago I had seen advertised online, but as I made my way up the last set of stairs I hit a roadblock. 

“Oh heyyy…” she screamed, sprawled out on the stairwell with a large bottle of vodka in her hand. 

She was about 5 foot, 3 inches, with long black hair, her large boobs nicely pushing out of a tight white shirt. 

She was in her forties but had the spirit of someone much younger. 

Her equally juiced friend beside her had blondish hair but apart from that small difference, they were practically the same off the shelf dishevelled cougars. 

They passed the bottle of vodka back and forth as I stood there. 

“Do you know what time it is?” Black Hair asked as she took another deep sip from the bottle. 

“420!” I said, still trying to get past them. 

“420, I like this guy.” she giggled like a schoolgirl. 

“We’re going to go to the pub across the street to drink some more, do you want to join us?” 

I was drunk in ten minutes. 

Blondish ordered calamari for the table, I had never come across the stuff before. Squid, fried squid, ‘Sounds disgusting.’ I thought, it turned out to be delicious. 

I was more interested in my new found love of calamari than the middle-aged woman I was sharing it with until Blondish went to the bathroom and left me all alone with Black Hair. 

Was I drunk enough yet? Drunk enough to sleep with this mess? 

Somewhere inside myself – …probably somewhere inside my dick… – answered… 

YES! 

I was drunk and happy, calamari happy. 

I made my move on Black Hair and it landed. 

“WHAT ARE YOU DOING? SHE HAS A FIANCÉ!” I heard her friend shout across the pub while my tongue was making its way down Black Hair’s throat. 

Everyone in the pub heard. I took my tongue out of Black Hair’s mouth and looked bemused at her friend’s reappearance, although she had shouted it so the world could hear, it was a casual shout, an expectant tone. 

‘She said that so casually.’ I thought to myself. 

We had sex in Black Hair’s tiny private room back at the hostel. Sexcapades interrupted briefly by a call from her Marine fiancé and another from her adult son. 

I lost one of my socks during the session which was annoying, I didn’t have many socks. 

Chicago was smiling kindly on me though, and that afternoon wouldn’t be the wildest time I had in Wicker Park either. 

_ 

She looked sweet and religious at first, she was traveling with a French guy who appeared to be her boyfriend but soon revealed himself to be a lovesick fool financing her hopes of becoming a professional ballerina. 

I was relaxing on the sofa in the lounge when I began to talk to her about what had happened on my first day at the hostel. 

I told her the tale of Black Hair, her friend Blondish and my eventful afternoon. 

The more I talked to her, the more she seemed like a psychopath. Then again, my stories probably led her to think the same thing of me. 

“Have you ever had an orgy?” she asked me, eyes wide open.  

A while later Black Hair and Blondish joined the conversation as well as a couple of Australian guys and Tommy, a gay American who was a fixture of the hostel, always flamboyant and always lovely. 

Nobody really needed to say it, it was already on the schedule for all of us now. A nice winter orgy in Chicago was up next. 

We arranged the logistics of the orgy and an hour later we had a room booked for me, Black Hair, Not So Innocent Ballerina, the two Australians and Tommy. Tommy wasn’t going to be involved in the proceedings but came along anyway. Blondish for some reason declined to participate. 

The room had a large double bed in front of the windows on the far side, a comfortable looking chair beside the bed and a set of bunk beds against the wall by the door. 

Tommy undressed in the corner and claimed the chair by the bed, and with nothing else to do, masterbated away. 

I woke up the next morning after the fog of an hour’s sleep to an emptying room. 

I got dressed to disturbing flashes of strange cocks and balls and vaginas and arseholes. 

I woke one of the Australians up and we left the room for an early morning breakfast. 

Two strangers who had just been involved in some international gang banging together eating eggs and sipping coffee at a small table in the middle of a Chicago diner. It was less awkward than it probably should have been. 

It took awhile to get my energy back, after sleeping back at the hostel for a few hours, I woke in the late afternoon and ran into Not So Innocent Ballerina. 

We went into downtown Chicago on a shopping trip. It felt a bit weird going on what felt like an innocent first date after being fellow participants in an orgy. 

We walked around the skyscraper lined streets, ate Subway and went shoe shopping. 

I needed a new pair of something, so I didn’t protest at what in this world and every damn world is usually pure torture, shoe shopping with a woman. 

I bought a new pair of high top Converse. I made the pick in minutes and then left Not So Innocent Ballerina behind in the store to debate with herself what to buy. Date over. 

I wasn’t in love with her, not even close. No need to punish myself, that’s what her lovesick fool was for. 

This purchase kick-started a shopping spree over the next few days that culminated in the purchase of a $400 leather jacket that I was incredibly happy with. 

I looked COOL as FUCK and everybody knew it. 

I would strut like a fucking queen every day across the street and into my new favourite thing in the universe. Potbelly Sandwich Shop. Oh baby. Potbelly Sandwich Shop. 

The post orgy hangover was now fully over. I had the motherfucking boosters on. 

My new expensive jacket. My perfect shoes. My stomach full of fuck loads of Potbelly sandwiches…

…and I was out into the labyrinth of the hostel again. 

The orgy crowd cleared out and the magic melting pot of Chicago conjured up new characters to replace them. 

Back in the labyrinth I met a friendly photographer and artist, Mola from Chile. 

Mola was short and chubby with a goth girl look and a cute, verging on pretty face. 

Soon after meeting her, Mola revealed a nice big camera with even bigger lenses so we went up to the rooftop and had a photoshoot. 

I had sold my DSLR camera for the ticket to America and was relying solely on my ageing iPhone 4S to capture the journey. 

I sweet talked her into it. A professional camera with the backdrop of Chicago, I wasn’t missing that opportunity. 

A lot of strange scenes played out with Mola. 

We took one of her paintings to a 7-Eleven for the clerk to buy, the scene had the trappings of a drug deal. 

We watched porn in the common room with a very nervous, constantly hazed by other guests Japanese guy. 

She gave me a hot drunken blowjob in the hostel bathroom. 

I threatened to break a guests neck when he called us fags for not wanting to go and get wasted. 

A lot of strange, interesting scenes. 

Early in the morning on one of these blurred together days after a sleepless night, me, Mola and our new friend – I’ll call her Red, since she had red hair – took the L to downtown for breakfast. 

Over the usual delicious McDonald’s crap we got into a conversation about life and travel. 

Mola talked of wanting to do everything in life. 

Red replied, “You shouldn’t want to do everything, you just have to make great life choices.” 

Those words stuck with me, a beautiful thing to say, kind of perfect. 

I could have done a lot of different things in all the countries I’d been to, but there was nothing to regret, I did what I did and had my fun and I’d continue that way. 

She deserves more than Red, The McDonald’s Preacher, or The Illinois McBreakfast Sage Fairy perhaps. 

Mola left and Red left too and for the first time I was all alone in the hostel. 

Maybe I was getting exhausted from it all. Chicago had supplied me with a raging river of characters and too many stories in such a short period of time. 

But. I still had some more time in Chi and just enough reserves in me for one more jump into the swirling pool of hostel potential. 

So that’s what I did, I jumped back into the swirling pool of hostel potential and found my final characters of Chicagoland and my last great romance until Southern California.

_ 

She was My German lady and came with a free guy friend too. 

My German Lady and My Free Guy Friend were travelling around Canada and the US in a car for fun and this guy friend of hers was actually a really nice person, all friendly and sweet. 

It was obvious he was in love with her and that the love had been unrequited for quite some time. 

I met them one afternoon up on the rooftop. I was smoking away, deep in thought, the cold wind hitting me from all directions, then the German language started floating about. 

I ignored the unwanted interruption. 

The sounds of German on the cold wind dissipated and I turned my head to take a look at what had been producing them. 

‘She’s next then.’ I thought, as I saw them standing by the door. 

I turned back to face the skyscrapers and ate a few more bites of nicotine. 

My German Lady was about five foot, four inches with light blonde hair and pretty features. Her guy friend was nondescript… alright, I’ll try. An average Europeany male with a tan? 

My German Lady was popular with the male guests of the hostel. She would walk into a room and have several men pounce on her within seconds. 

I didn’t completely understand it, she was definitely attractive, but by no means jump off a bridge after running through fire attractive. Not even get up off the coach and interrupt this Politico article attractive. 

My coldness and nonchalance most likely contributed to her falling for me so hard. 

The main reasons she pushed the other guys aside and focused all her energy on me so quickly. 

I knew she liked me, so I decided to make the chase even more frustrating and thrilling for her. 

I stretched the timeline out further and further until she had thrown aside all distractions, all the excess male attention and her male friend and was verging on a psychotic break. 

After a long three days, she finally had me alone on the rooftop. 

The skyscrapers on the skyline watched on with bated breath. 

I kissed her. She melted. 

Later that night we had the most uncomfortable fuck in history in one of the hostel shower rooms. 

The tiles dug into my back, my legs pressed against the wall at an awkward angle. I was all squashed up, some mangled form. I gritted my teeth. The hot blonde German rode me up and down at a furious pace. 

We tried our best to find a position to fuck properly. We never found it. Even standing was a problem, thanks to the weirdly shaped and slippery floor. 

A solid hour of stressful fucking ended in two collapsed, exhausted, piles of flesh looking like they needed an ambulance. 

On our one big outing together we climbed the Sears Tower – It will always be the Sears Tower and not the boring thing they renamed it. 

I never had a list of things to do or attractions I had to see, and because of that I didn’t get around to doing these kinds of things too often. Maybe I should have been a better tourist. I was always an awful one. Still am. 

When My German Lady suggested it, I even tried to convince her, let’s not. 

The view of the sunset from the top, spreading threads of golden light over the entire city was beautiful though. 

Chicago was a feeling, a majestic feeling, and very American.

If I were to choose the capital of the United States of America I wouldn’t stick it between Maryland and Virginia, it wouldn’t be Washington DC. I’d place it there on Lake Michigan. It would be Chicago. 

_ 

My new $400 leather jacket and pair of converses, the potbelly sandwiches, the endless supply of romance, the freezing air and the friendly people. 

I felt at home in Chicago. 

On the last day, I made it onto the California Zephyr with minutes to spare and despite the journey ahead west to California, there was a lot of me that wanted to stay. 

I was daydreaming of the possibilities. I’d buy a loft somewhere, have my local bar and a group of weirdos to be weird with and have more fun than I could contain in any book chapter. 

There were too many other places I could say those same things about though, so I kept moving.